I honestly think a time skip would be good.

Because it would organize everybody AND offer a chance to become acquaintances during the time skip, defeating the need to reintroduce yourself time and time again. It'd be cool with a two week timeskip and everyone is like several levels higher and knows most of each other either personally or via rumours. 

It will make it a lot more easier to get to the raid on the level 1 boss. Like, timeskip right into the meeting the day before we commence the raid and everyone is having dinner together in town. Just a suggestion though.

Cuz its been 111 posts and we've barely gone anywhere for some of us >_>".